A green and efficient photo-driven route for the selective oxidation of aqueous isopropanol solution to pinacol (C6) with hydrogen peroxide

被引:5
作者
Li, Na [1 ]
Yan, Wenjun [1 ]
Zhang, Hongxia [1 ,2 ]
Jia, Suping [1 ]
Wang, Zhijian [1 ]
Zheng, Jianfeng [1 ]
Zhu, Zhenping [1 ]
机构
[1] Chinese Acad Sci, Inst Coal Chem, State Key Lab Coal Convers, Taiyuan 030001, Shanxi, Peoples R China
[2] Shanxi Univ, Inst Applicat Chem, Taiyuan 030001, Peoples R China
基金
中国国家自然科学基金;
关键词
CARBON BOND FORMATION; VISIBLE-LIGHT; ALIPHATIC-ALCOHOLS; ARYL ALDEHYDES; KETONES; WATER; PHOTOCATALYSTS; TRANSFORMATION; IRRADIATION; SYSTEM;
D O I
10.1039/c6nj03848d
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Selective oxidation of alcohols to highly valued chemicals in a clean manner (e.g., with water as a solvent and O-2 or H2O2 as the primary oxidant) is the subject of considerable research attention. This paper presents a simple and environmentally friendly approach for the selective oxidation of isopropanol to pinacol C-6 (2,3-dimethyl-2,3-butanediol) in water with hydrogen peroxide (H2O2) through UV irradiation under mild conditions. A selectivity of 82-95% is achieved at H2O2 feeding rates below 4 mL h(-1). The introduction of TiO2 nanotubes can further accelerate isopropanol conversion and enhance pinacol C-6 formation. The highest formation rate of pinacol C-6 and the highest conversion rate of isopropanol are 29.4 and 71.4 mmol h(-1), respectively. The proposed strategy provides a green solution for the synthesis of aliphatic pinacol and offers a new design for the construction of C-C bonds with alphatic alcohol.
引用
收藏
页码:2764 / 2768
页数:5
相关论文
共 31 条
[1]   Alcohol-Selective Oxidation in Water under Mild Conditions via a Novel Approach to Hybrid Composite Photocatalysts [J].
Abd-Elaal, Ali ;
Parrino, Francesco ;
Ciriminna, Rosaria ;
Loddo, Vittorio ;
Palmisano, Leonardo ;
Pagliaro, Mario .
CHEMISTRYOPEN, 2015, 4 (06) :779-785
[2]   Simple and expeditious pinacol coupling of non usual α,β-unsaturated carbonyl compounds in water [J].
Billamboz, Muriel ;
Sotto, Nicolas ;
Chevrin-Villette, Carole ;
Len, Christophe .
RSC ADVANCES, 2015, 5 (57) :46026-46030
[3]   Amide-directed photoredox-catalysed C-C bond formation at unactivated sp3 C-H bonds [J].
Chu, John C. K. ;
Rovis, Tomislav .
NATURE, 2016, 539 (7628) :272-275
[4]   Photocatalytic Oxidation of Alcohols over TiO2 Covered with Nb2O5 [J].
Furukawa, Shinya ;
Shishido, Tetsuya ;
Teramura, Kentaro ;
Tanaka, Tsunehiro .
ACS CATALYSIS, 2012, 2 (01) :175-179
[5]   A catalytic system consisting of vanadium, chlorosilane, and aluminum metal in the stereoselective pinacol coupling reaction of benzaldehyde derivatives [J].
Hirao, T ;
Hatano, B ;
Imamoto, Y ;
Ogawa, A .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (20) :7665-7667
[6]   Oxidation of aliphatic alcohols and benzyl alcohol by H2O2 under the hydrothermal conditions in the presence of solid-state catalysts using batch and flow reactors [J].
Kawamura, Kunio ;
Yasuda, Tomoko ;
Hatanaka, Tsubasa ;
Hamahiga, Kazuhiro ;
Matsuda, Nami ;
Ueshima, Michio ;
Nakai, Kazuyuki .
CHEMICAL ENGINEERING JOURNAL, 2016, 285 :49-56
[7]   Dual enantioselective control in asymmetric synthesis [J].
Kim, YH .
ACCOUNTS OF CHEMICAL RESEARCH, 2001, 34 (12) :955-962
[8]   Electrochemical pinacol coupling of aromatic carbonyl compounds in a [BMIM][BF4]-H2O mixture [J].
Kronenwetter, Hannah ;
Husek, Jakub ;
Etz, Brian ;
Jones, Aaron ;
Manchanayakage, Renuka .
GREEN CHEMISTRY, 2014, 16 (03) :1489-1495
[9]   Metal-catalyzed epoxidations of alkenes with hydrogen peroxide [J].
Lane, BS ;
Burgess, K .
CHEMICAL REVIEWS, 2003, 103 (07) :2457-2473
[10]   Manganese-mediated carbon-carbon bond formation in aqueous media: Chemoselective allylation and pinacol coupling of aryl aldehydes [J].
Li, CJ ;
Meng, Y ;
Yi, XH ;
Ma, JH ;
Chan, TH .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (21) :7498-7504